TWI659973B - Light and moisture curing resin composition, adhesive for electronic parts, and adhesive for display elements - Google Patents
Light and moisture curing resin composition, adhesive for electronic parts, and adhesive for display elements Download PDFInfo
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- TWI659973B TWI659973B TW103135917A TW103135917A TWI659973B TW I659973 B TWI659973 B TW I659973B TW 103135917 A TW103135917 A TW 103135917A TW 103135917 A TW103135917 A TW 103135917A TW I659973 B TWI659973 B TW I659973B
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- TW
- Taiwan
- Prior art keywords
- moisture
- light
- resin composition
- curable resin
- meth
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 105
- 239000000853 adhesive Substances 0.000 title claims abstract description 22
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 22
- 238000013008 moisture curing Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000000945 filler Substances 0.000 claims abstract description 30
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 19
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 9
- -1 amine ester Chemical class 0.000 claims description 94
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- ZBKFYXZXZJPWNQ-UHFFFAOYSA-N isothiocyanate group Chemical group [N-]=C=S ZBKFYXZXZJPWNQ-UHFFFAOYSA-N 0.000 claims description 15
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 14
- 239000011164 primary particle Substances 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 9
- 235000012239 silicon dioxide Nutrition 0.000 claims description 8
- 230000005661 hydrophobic surface Effects 0.000 claims description 5
- 239000000516 sunscreening agent Substances 0.000 claims description 5
- 238000004381 surface treatment Methods 0.000 claims description 5
- 230000000475 sunscreen effect Effects 0.000 claims description 4
- 239000011256 inorganic filler Substances 0.000 claims description 2
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 abstract description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 81
- 239000003822 epoxy resin Substances 0.000 description 31
- 229920000647 polyepoxide Polymers 0.000 description 31
- 229920005862 polyol Polymers 0.000 description 29
- 239000004593 Epoxy Substances 0.000 description 21
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 150000003077 polyols Chemical class 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 17
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 229910052719 titanium Inorganic materials 0.000 description 16
- 239000010936 titanium Substances 0.000 description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000000126 substance Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 6
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000004843 novolac epoxy resin Substances 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- MUBQKSBEWRYKES-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO MUBQKSBEWRYKES-UHFFFAOYSA-N 0.000 description 2
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 2
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 description 2
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
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- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 2
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- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 2
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
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- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
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Abstract
本發明之目的在於提供一種形狀保持性、接著性、速硬化性、及塗佈性優異之光與溼氣硬化型樹脂組成物。又，本發明之目的在於提供一種使用該光與溼氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 An object of the present invention is to provide a light and moisture-curable resin composition excellent in shape retention, adhesion, rapid curing, and coatability. Another object of the present invention is to provide an adhesive for electronic parts and an adhesive for display elements using the light and moisture-curable resin composition.
本發明係一種光與溼氣硬化型樹脂組成物，其含有自由基聚合性化合物、溼氣硬化型胺酯樹脂(urethane resin)、光自由基聚合起始劑、及填充劑。 The present invention is a light and moisture-curable resin composition containing a radical polymerizable compound, a moisture-curable urethane resin, a photo-radical polymerization initiator, and a filler.
Description
本發明係關於一種形狀保持性、接著性、速硬化性、及塗佈性優異之光與溼氣硬化型樹脂組成物。又，本發明係關於一種使用該光與溼氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 The present invention relates to a light- and moisture-curable resin composition having excellent shape retention, adhesion, rapid curing, and coating properties. The present invention also relates to an adhesive for electronic parts and an adhesive for display elements using the light and moisture-curable resin composition.
近年來，作為具有薄型、輕量、低耗電等特徵之顯示元件，廣泛地利用液晶顯示元件或有機EL顯示元件等。該等顯示元件中，液晶或發光層之密封、基板、光學膜、保護膜或各種構件之接著等通常使用光硬化型樹脂組成物。 In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having characteristics such as thinness, light weight, and low power consumption. Among these display elements, a light-curable resin composition is usually used for sealing of a liquid crystal or a light-emitting layer, bonding of a substrate, an optical film, a protective film, or various members.
且說，於行動電話、攜帶型遊戲機等各種附帶顯示元件之移動裝置普及之現代社會，顯示元件之小型化為最迫切之課題，作為小型化之方法，已進行將圖像顯示部窄邊緣化(以下，亦稱作窄邊緣設計)。然而，於窄邊緣設計中，有於光無法充分到達之部分塗佈有光硬化型樹脂組成物之情況，結果有塗佈於光無法到達之部分之光硬化型樹脂組成物的硬化不足夠之問題。因此，亦進行使用光熱硬化型樹脂組成物作為即便於塗佈在光無法到達之部分之情形時亦可充分地硬化之樹脂組成物，而併用光硬化與熱硬化，但有因高溫下之加熱而對元件等造成不良影響之虞。 Furthermore, in a modern society where mobile devices with display elements such as mobile phones and portable game consoles are widespread, miniaturization of display elements is the most urgent issue. As a method of miniaturization, narrowing of the image display portion has been performed. (Hereinafter also referred to as narrow edge design). However, in the narrow-edge design, the light-curable resin composition may be applied to a portion where light cannot be sufficiently reached, and as a result, the light-curable resin composition applied to a portion where light cannot be reached may be insufficiently cured. problem. Therefore, a photothermosetting resin composition is also used as a resin composition that can be sufficiently cured even when it is applied to a portion where light cannot reach, and photocuring and thermal curing are used in combination. It may cause adverse effects on components and the like.
作為不進行高溫加熱而使樹脂組成物硬化之方法，於專利文獻1中，揭示有如下方法：使用含有分子中具有至少1個異氰酸酯基與至 少1個(甲基)丙烯醯基之胺酯預聚物的光與溼氣硬化型樹脂組成物，而併用光硬化與溼氣硬化。然而，於使用如專利文獻1中所揭示之光與溼氣硬化型樹脂組成物之情形時，存在如下問題：塗佈後之樹脂組成物會擴展而無法保持形狀，或於接著基板等被接著體時之接著性不充分。 As a method for curing the resin composition without performing high-temperature heating, Patent Document 1 discloses a method of using a resin containing at least one isocyanate group and A light and moisture-curable resin composition having at least one (meth) acrylfluorenyl amine ester prepolymer, and a combination of light and moisture curing. However, in the case of using the light and moisture-curable resin composition as disclosed in Patent Document 1, there are problems in that the resin composition after application expands and cannot maintain the shape, or is adhered to a substrate or the like. Adequacy of body adhesion.
專利文獻1：日本特開2008-274131號公報 Patent Document 1: Japanese Patent Application Laid-Open No. 2008-274131
本發明之目的在於提供一種形狀保持性、接著性、速硬化性、及塗佈性優異之光與溼氣硬化型樹脂組成物。又，本發明之目的在於提供一種使用該光與溼氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 An object of the present invention is to provide a light and moisture-curable resin composition excellent in shape retention, adhesion, rapid curing, and coatability. Another object of the present invention is to provide an adhesive for electronic parts and an adhesive for display elements using the light and moisture-curable resin composition.
本發明係一種光與溼氣硬化型樹脂組成物，其含有自由基聚合性化合物、溼氣硬化型胺酯樹脂(urethane resin)、光自由基聚合起始劑、及填充劑。 The present invention is a light and moisture-curable resin composition containing a radical polymerizable compound, a moisture-curable urethane resin, a photo-radical polymerization initiator, and a filler.
以下，詳細敍述本發明。 Hereinafter, the present invention will be described in detail.
本發明者等人認為習知之光與溼氣硬化型樹脂組成物中接著性不足之原因在於，具有光硬化性與溼氣硬化性兩者之胺酯預聚物之光硬化性過高，而研究藉由使用自由基聚合性化合物、速硬化性優異之溼氣硬化型胺酯樹脂、及光自由基聚合起始劑，而調整光硬化性與溼氣硬化性以提高接著性。然而，即便使用此種光與溼氣硬化型樹脂組成物，亦存在無法充分地保持塗佈後之形狀之情況。因此，本發明者等人發現藉由於此種光與溼氣硬化型樹脂組成物中進而調配填充劑，可獲得形狀保持性、接著性、速硬化性、及塗佈性均優異之光與溼氣硬化型樹脂組成物，從而完成本發明。 The present inventors believe that the reason why the conventional light and moisture-curable resin composition has insufficient adhesion is that the amine ester prepolymer having both light-curability and moisture-curability is too high in light-curability, and The use of a radically polymerizable compound, a moisture-curable urethane resin having excellent rapid curing properties, and a photo-radical polymerization initiator have been studied to improve the photo-curability and moisture-curability to improve adhesion. However, even if such a light- and moisture-curable resin composition is used, the shape after coating may not be sufficiently maintained. Therefore, the present inventors have found that by blending fillers in such a light- and moisture-curable resin composition, light and moisture that are excellent in shape retention, adhesion, rapid curing, and coating properties can be obtained. The gas-curable resin composition has completed the present invention.
本發明之光與溼氣硬化型樹脂組成物含有自由基聚合性化 合物。 The light and moisture-curable resin composition of the present invention contains a radical polymerizable polymer 组合。 The compound.
作為上述自由基聚合性化合物，只要為具有光聚合性之自由基聚合性化合物即可，且只要為分子中具有自由基反應性官能基之化合物，則無特別限定，但較佳為具有不飽和雙鍵作為自由基反應性官能基之化合物，尤其就反應性之方面而言，較佳為具有(甲基)丙烯醯基之化合物(以下，亦稱作「(甲基)丙烯酸化合物」)。 The radical polymerizable compound is not particularly limited as long as it is a photopolymerizable radical polymerizable compound, and it is a compound having a radical reactive functional group in the molecule, but it is preferably unsaturated The compound having a double bond as a radical-reactive functional group is particularly preferably a compound having a (meth) acrylfluorenyl group (hereinafter, also referred to as "(meth) acrylic compound") in terms of reactivity.
再者，於本說明書中，上述「(甲基)丙烯醯基」意指丙烯醯基或甲基丙烯醯基，上述「(甲基)丙烯酸」意指丙烯酸或甲基丙烯酸。 In addition, in the present specification, the "(meth) acrylfluorenyl" means acrylfluorenyl or methacrylfluorenyl, and the "(meth) acryl" means acrylic acid or methacrylic acid.
作為上述(甲基)丙烯酸化合物，例如可列舉：藉由使(甲基)丙烯酸與具有羥基之化合物反應而獲得之酯化合物、藉由使(甲基)丙烯酸與環氧化合物反應而獲得之環氧(甲基)丙烯酸酯、藉由使異氰酸酯與具有羥基之(甲基)丙烯酸衍生物反應而獲得之(甲基)丙烯酸胺酯等。 Examples of the (meth) acrylic compound include an ester compound obtained by reacting (meth) acrylic acid with a compound having a hydroxyl group, and a ring obtained by reacting (meth) acrylic acid with an epoxy compound. Oxygen (meth) acrylate, amine (meth) acrylate obtained by reacting an isocyanate with a (meth) acrylic acid derivative having a hydroxyl group, and the like.
再者，於本說明書中，所謂上述「(甲基)丙烯酸酯」，意指丙烯酸酯或甲基丙烯酸酯。又，成為上述(甲基)丙烯酸胺酯之原料之異氰酸酯之異氰酸酯基全部用於胺酯鍵之形成，上述(甲基)丙烯酸胺酯不具有殘留異氰酸酯基。 In addition, in this specification, the "(meth) acrylate" means an acrylate or a methacrylate. In addition, all isocyanate groups of the isocyanate which is the raw material of the amine (meth) acrylate are used for the formation of amine ester bonds, and the methacrylate (meth) acrylate does not have a residual isocyanate group.
作為上述酯化合物中之單官能者，例如可列舉：N-丙烯醯氧基乙基六氫鄰苯二甲醯亞胺等鄰苯二甲醯亞胺丙烯酸酯類或各種醯亞胺丙烯酸酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸十八烷基酯、(甲基)丙烯酸異莰基酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-甲氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸四氫呋喃甲酯、(甲基)丙烯酸苄酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚 乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、醯亞胺(甲基)丙烯酸酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸十四烷基酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸雙環戊烯酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸二乙胺基乙酯、(甲基)丙烯酸二甲胺基乙酯、琥珀酸2-(甲基)丙烯醯氧基乙酯、六氫鄰苯二甲酸2-(甲基)丙烯醯氧基乙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基2-羥基丙酯、(甲基)丙烯酸環氧丙酯、磷酸2-(甲基)丙烯醯氧基乙酯等。 Examples of the monofunctional compound in the above-mentioned ester compounds include phthalimide acrylates such as N-acryloxyethylhexahydrophthalimide, various acetimide acrylates, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, isopropyl (meth) acrylate Butyl, tert-butyl (meth) acrylate, isooctyl (meth) acrylate, dodecyl (meth) acrylate, octadecyl (meth) acrylate, isopropyl (meth) acrylate Fluorenyl ester, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate Ester, tetrahydrofuran methyl (meth) acrylate, benzyl (meth) acrylate, ethyl carbitol (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol ( (Meth) acrylate, phenoxy poly Ethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3 1,3-tetrafluoropropyl, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, ammonium (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, N-butyl (meth) acrylate, propyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isononyl (meth) acrylate, (methyl) Tetradecyl acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, dicyclopentenyl (meth) acrylate, isomethacrylate (meth) acrylate Decyl ester, diethylaminoethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, 2- (meth) acryloxyethyl succinate, hexahydrophthalate 2- (Meth) acryloxyethyl, 2- (meth) acryloxyethyl 2-hydroxypropyl phthalate, glycidyl (meth) acrylate, 2- (methyl) phosphate Propylene ethoxylate and the like.
又，作為上述酯化合物中之2官能者，例如可列舉：1,4-丁二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、環氧丙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚A二(甲基)丙烯酸酯、環氧乙烷加成雙酚F二(甲基)丙烯酸酯、二(甲基)丙烯酸二羥甲基二環戊二烯酯、1,3-丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、環氧乙烷改質異三聚氰酸二(甲基)丙烯酸酯、(甲基)丙烯酸2-羥基-3-(甲基)丙烯醯氧基丙酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己內酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。 Moreover, as a bifunctional one among the said ester compounds, 1, 4- butanediol di (meth) acrylate, 1, 3- butanediol di (meth) acrylate, 1,6- Hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, 2-n-butyl-2-ethyl -1,3-propanediol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene glycol di (methyl) Acrylate), diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene oxide addition bisphenol A di (Meth) acrylate, ethylene oxide addition bisphenol A di (meth) acrylate, ethylene oxide addition bisphenol F di (meth) acrylate, di (meth) acrylate dihydroxymethyl Dicyclopentadiene ester, 1,3-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified isotrimeric cyanuric acid di (methyl) ) Acrylic acid ester, 2-hydroxy-3- (meth) acrylic acid oxypropyl (meth) acrylate, carbonate diol Di (meth) acrylate, polyetherdiol di (meth) acrylate, polyesterdiol di (meth) acrylate, polycaprolactonediol di (meth) acrylate, polybutadiene Glycol di (meth) acrylate and the like.
又，作為上述酯化合物中之3官能以上者，例如可列舉：新戊四醇三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、環氧丙烷加成 三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成三羥甲基丙烷三(甲基)丙烯酸酯、己內酯改質三羥甲基丙烷三(甲基)丙烯酸酯、環氧乙烷加成異三聚氰酸三(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯、二-三羥甲基丙烷四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、環氧丙烷加成甘油三(甲基)丙烯酸酯、磷酸三(甲基)丙烯醯氧基乙酯等。 In addition, examples of the tri- or more functional group among the above-mentioned ester compounds include neopentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, and propylene oxide addition. Trimethylolpropane tri (meth) acrylate, ethylene oxide addition trimethylolpropane tri (meth) acrylate, caprolactone modified trimethylolpropane tri (meth) acrylate, Ethylene oxide addition tris (meth) acrylate isotrimeric cyanate, penta (meth) acrylate dipentaerythritol, hexa (meth) acrylate dipentaerythritol, di-trimethylol Propane tetra (meth) acrylate, neopentaerythritol tetra (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide addition glycerol tri (meth) acrylate, tris (methyl) phosphate ) Acrylic ethoxyethyl and the like.
作為上述環氧(甲基)丙烯酸酯，例如可列舉藉由依照常規方法使環氧化合物與(甲基)丙烯酸於鹼性觸媒之存在下反應而獲得者等。 Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst in accordance with a conventional method.
作為成為用以合成上述環氧(甲基)丙烯酸酯之原料之環氧化合物，例如可列舉：雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、2,2'-二烯丙基雙酚A型環氧樹脂、氫化雙酚型環氧樹脂、環氧丙烷加成雙酚A型環氧樹脂、間苯二酚型環氧樹脂、聯苯型環氧樹脂、硫化物型環氧樹脂、二苯醚型環氧樹脂、二環戊二烯型環氧樹脂、萘型環氧樹脂、苯酚酚醛清漆型環氧樹脂、鄰甲酚酚醛清漆型環氧樹脂、二環戊二烯酚醛清漆型環氧樹脂、聯苯酚醛清漆型環氧樹脂、萘酚酚醛清漆型環氧樹脂、環氧丙胺型環氧樹脂、烷基多元醇型環氧樹脂、橡膠改質型環氧樹脂、環氧丙酯化合物、雙酚A型環硫樹脂等。 Examples of the epoxy compound used as a raw material for synthesizing the aforementioned epoxy (meth) acrylate include bisphenol A-type epoxy resin, bisphenol F-type epoxy resin, bisphenol S-type epoxy resin, 2 , 2'-diallyl bisphenol A epoxy resin, hydrogenated bisphenol epoxy resin, propylene oxide addition bisphenol A epoxy resin, resorcinol epoxy resin, biphenyl ring Oxygen resin, sulfide epoxy resin, diphenyl ether epoxy resin, dicyclopentadiene epoxy resin, naphthalene epoxy resin, phenol novolac epoxy resin, o-cresol novolac epoxy resin Resin, dicyclopentadiene novolac epoxy resin, biphenol novolac epoxy resin, naphthol novolac epoxy resin, epoxy amine epoxy resin, alkyl polyol epoxy resin, rubber Modified epoxy resin, propylene oxide ester compound, bisphenol A episulfide resin, etc.
作為上述雙酚A型環氧樹脂中之市售者，例如可列舉jER828EL、jER1001、jER1004(均為三菱化學公司製造)、EPICLON 850-S(DIC公司製造)等。 Examples of commercially available bisphenol A-type epoxy resins include jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation), EPICLON 850-S (manufactured by DIC Corporation), and the like.
作為上述雙酚F型環氧樹脂中之市售者，例如可列舉jER806、jER4004(均為三菱化學公司製造)等。 Examples of a commercially available bisphenol F-type epoxy resin include jER806 and jER4004 (both manufactured by Mitsubishi Chemical Corporation).
作為上述雙酚S型環氧樹脂中之市售者，例如可列舉EPICLON EXA1514(DIC公司製造)等。 Examples of a commercially available bisphenol S-type epoxy resin include EPICLON EXA1514 (manufactured by DIC Corporation).
作為上述2,2'-二烯丙基雙酚A型環氧樹脂中之市售者，例如可列舉 RE-810NM(日本化藥公司製造)等。 As a marketer among the 2,2'-diallyl bisphenol A type epoxy resins, for example, RE-810NM (manufactured by Nippon Kayaku Co., Ltd.) and the like.
作為上述氫化雙酚型環氧樹脂中之市售者，例如可列舉EPICLON EXA7015(DIC公司製造)等。 As a commercial one among the said hydrogenated bisphenol-type epoxy resins, Epiclon EXA7015 (made by DIC Corporation) etc. are mentioned, for example.
作為上述環氧丙烷加成雙酚A型環氧樹脂中之市售者，例如可列舉EP-4000S(ADEKA公司製造)等。 Examples of a commercially available propylene oxide-added bisphenol A type epoxy resin include EP-4000S (manufactured by ADEKA).
作為上述間苯二酚型環氧樹脂中之市售者，例如可列舉EX-201(Nagase chemteX公司製造)等。 As a marketer among the said resorcinol-type epoxy resins, EX-201 (made by Nagase chemteX company) etc. are mentioned, for example.
作為上述聯苯型環氧樹脂中之市售者，例如可列舉jER YX-4000H(三菱化學公司製造)等。 Examples of a commercially available biphenyl type epoxy resin include jER YX-4000H (manufactured by Mitsubishi Chemical Corporation).
作為上述硫化物型環氧樹脂中之市售者，例如可列舉YSLV-50TE(新日鐵住金化學公司製造)等。 As a commercially available one among the said sulfide-type epoxy resins, YSLV-50TE (made by Nippon Steel & Sumitomo Chemical Co., Ltd.) etc. are mentioned, for example.
作為上述二苯醚型環氧樹脂中之市售者，例如可列舉YSLV-80DE(新日鐵住金化學公司製造)等。 Examples of a commercially available diphenyl ether type epoxy resin include YSLV-80DE (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.).
作為上述二環戊二烯型環氧樹脂中之市售者，例如可列舉EP-4088S(ADEKA公司製造)等。 Examples of a commercially available dicyclopentadiene-type epoxy resin include EP-4088S (manufactured by ADEKA).
作為上述萘型環氧樹脂中之市售者，例如可列舉EPICLON HP4032、EPICLON EXA-4700(均為DIC公司製造)等。 Examples of the commercially available naphthalene-type epoxy resin include EPICLON HP4032 and EPICLON EXA-4700 (both manufactured by DIC Corporation).
作為上述苯酚酚醛清漆型環氧樹脂中之市售者，例如可列舉EPICLON N-770(DIC公司製造)等。 As a commercially available one among the said phenol novolak-type epoxy resins, Epiclon N-770 (made by DIC Corporation) etc. are mentioned, for example.
作為上述鄰甲酚酚醛清漆型環氧樹脂中之市售者，例如可列舉EPICLON N-670-EXP-S(DIC公司製造)等。 Examples of the commercially available o-cresol novolac-type epoxy resin include EPICLON N-670-EXP-S (manufactured by DIC Corporation) and the like.
作為上述二環戊二烯酚醛清漆型環氧樹脂中之市售者，例如可列舉EPICLON HP7200(DIC公司製造)等。 Examples of a commercially available dicyclopentadiene novolac epoxy resin include EPICLON HP7200 (manufactured by DIC Corporation).
作為上述聯苯酚醛清漆型環氧樹脂中之市售者，例如可列舉NC-3000P(日本化藥公司製造)等。 As a commercially available one among the above-mentioned biphenol novolak-type epoxy resins, NC-3000P (made by Nippon Kayaku Co., Ltd.) is mentioned, for example.
作為上述萘酚酚醛清漆型環氧樹脂中之市售者，例如可列舉ESN-165S(新日鐵住金化學公司製造)等。 As a marketer of the said naphthol novolak-type epoxy resin, ESN-165S (made by Nippon Steel & Sumitomo Chemical Co., Ltd.) etc. are mentioned, for example.
作為上述環氧丙胺型環氧樹脂中之市售者，例如可列舉jER630(三菱化學公司製造)、EPICLON 430(DIC公司製造)、TETRAD-X(三菱瓦斯化學公司製造)等。 Examples of the commercially available epoxy amine type epoxy resin include jER630 (manufactured by Mitsubishi Chemical Corporation), EPICLON 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Corporation), and the like.
作為上述烷基多元醇型環氧樹脂中之市售者，例如可列舉ZX-1542(新日鐵住金化學公司製造)、EPICLON 726(DIC公司製造)、Epolight 80MFA(共榮社化學公司製造)、Denacol EX-611(Nagase chemteX公司製造)等。 As a marketer of the above-mentioned alkyl polyol type epoxy resin, for example, ZX-1542 (manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), EPICLON 726 (manufactured by DIC Corporation), and Epolight 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.) are mentioned. , Denacol EX-611 (manufactured by Nagase chemteX) and the like.
作為上述橡膠改質型環氧樹脂中之市售者，例如可列舉YR-450、YR-207(均為新日鐵住金化學公司製造)、Epolead PB(Daicel化學工業公司製造)等。 Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), and Epolead PB (made by Daicel Chemical Industry Co., Ltd.).
作為上述環氧丙酯化合物中之市售者，例如可列舉Denacol EX-147(Nagase chemteX公司製造)等。 As a marketer among the said propylene oxide ester compounds, Denacol EX-147 (made by Nagase chemteX company) etc. are mentioned, for example.
作為上述雙酚A型環硫樹脂中之市售者，例如可列舉jER YL-7000(三菱化學公司製造)等。 Examples of a commercially available bisphenol A-type episulfide resin include jER YL-7000 (manufactured by Mitsubishi Chemical Corporation).
作為上述環氧樹脂中之其他市售者，例如可列舉YDC-1312、YSLV-80XY、YSLV-90CR(均為新日鐵住金化學公司製造)、XAC4151(旭化成公司製造)、jER1031、jER1032(均為三菱化學公司製造)、EXA-7120(DIC公司製造)、TEPIC(日產化學公司製造)等。 Examples of other commercially available epoxy resins include YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd.), XAC4151 (made by Asahi Kasei Corporation), jER1031, jER1032 (all (Manufactured by Mitsubishi Chemical Corporation), EXA-7120 (manufactured by DIC Corporation), TEPIC (manufactured by Nissan Chemical Corporation), etc.
作為上述環氧(甲基)丙烯酸酯中之市售者，例如可列舉：EBECRYL860、EBECRYL3200、EBECRYL3201、EBECRYL3412、EBECRYL3600、EBECRYL3700、EBECRYL3701、EBECRYL3702、EBECRYL3703、EBECRYL3800、EBECRYL6040、EBECRYL RDX63182(均為Daicel-Allnex公司製造)、EA-1010、EA-1020、EA-5323、EA-5520、EA-CHD、EMA-1020(均為新中村化學工業公司製造)、環氧酯M-600A、環氧酯40EM、 環氧酯70PA、環氧酯200PA、環氧酯80MFA、環氧酯3002M、環氧酯3002A、環氧酯1600A、環氧酯3000M、環氧酯3000A、環氧酯200EA、環氧酯400EA(均為共榮社化學公司製造)、Denacol Acrylate DA-141、Denacol Acrylate DA-314、Denacol Acrylate DA-911(均為Nagase chemteX公司製造)等。 As the marketers of the aforementioned epoxy (meth) acrylates, for example, EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3703, EBECRYL3800, EBECRYL6040, and EBECRYD Rcel63182 (Manufactured by the company), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin Nakamura Chemical Industry Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, Epoxy ester 70PA, epoxy ester 200PA, epoxy ester 80MFA, epoxy ester 3002M, epoxy ester 3002A, epoxy ester 1600A, epoxy ester 3000M, epoxy ester 3000A, epoxy ester 200EA, epoxy ester 400EA ( All are manufactured by Kyoeisha Chemical Co., Ltd.), Denacol Acrylate DA-141, Denacol Acrylate DA-314, Denacol Acrylate DA-911 (all manufactured by Nagase chemteX), and the like.
上述(甲基)丙烯酸胺酯例如可藉由使具有羥基之(甲基)丙烯酸衍生物與具有異氰酸酯基之化合物於觸媒量之錫系化合物存在下反應而獲得。 The (meth) acrylic acid amine ester can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with a compound having an isocyanate group in the presence of a catalyst-based tin-based compound.
作為成為上述(甲基)丙烯酸胺酯之原料之異氰酸酯，例如可列舉：異佛爾酮二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯(MDI)、氫化MDI、聚合MDI、1,5-萘二異氰酸酯、降莰烷二異氰酸酯、聯甲苯胺二異氰酸酯、苯二甲基二異氰酸酯(XDI)、氫化XDI、離胺酸二異氰酸酯、三苯甲烷三異氰酸酯、三(異氰酸酯基苯基)硫代磷酸酯、四甲基二甲苯二異氰酸酯、1,6,10-十一烷三異氰酸酯等。 Examples of the isocyanate used as a raw material of the amine (meth) acrylate include isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, and Methylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, ditoluidine diisocyanate , Xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) phosphorothioate, tetramethylxylene diisocyanate, 1,6, 10-undecane triisocyanate and the like.
又，作為上述異氰酸酯，例如亦可使用藉由乙二醇、甘油、山梨糖醇、三羥甲基丙烷、(聚)丙二醇、碳酸酯二醇、聚醚二醇、聚酯二醇、聚己內酯二醇等多元醇與過剩之異氰酸酯之反應而獲得之經鏈延長之異氰酸酯化合物。 In addition, as the isocyanate, for example, ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, and polyhexamethylene can be used. A chain-extended isocyanate compound obtained by reacting a polyhydric alcohol such as a lactone diol with an excess of isocyanate.
作為成為上述(甲基)丙烯酸胺酯之原料之具有羥基之(甲基)丙烯酸衍生物，例如可列舉：乙二醇、丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、聚乙二醇等二元醇之單(甲基)丙烯酸酯、或三羥甲基乙烷、三羥甲基丙烷、甘油等三元醇之單(甲基)丙烯酸酯或者二(甲基)丙烯酸酯、或雙酚A型環氧(甲基)丙烯酸酯等環氧(甲基)丙烯酸酯等。 Examples of the (meth) acrylic acid derivative having a hydroxyl group as a raw material of the (meth) acrylic acid amine ester include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, and 1, Mono (meth) acrylates of diols such as 4-butanediol and polyethylene glycol, or mono (meth) acrylates of diols such as trimethylolethane, trimethylolpropane, and glycerol Or an epoxy (meth) acrylate, such as a di (meth) acrylate, or a bisphenol A epoxy (meth) acrylate, etc.
作為上述(甲基)丙烯酸胺酯中之市售者，例如可列舉：M-1100、M-1200、M-1210、M-1600(均為東亞合成公司製造)、EBECRYL230、 EBECRYL270、EBECRYL4858、EBECRYL8402、EBECRYL8411、EBECRYL8412、EBECRYL8413、EBECRYL8804、EBECRYL8803、EBECRYL8807、EBECRYL9260、EBECRYL1290、EBECRYL5129、EBECRYL4842、EBECRYL210、EBECRYL4827、EBECRYL6700、EBECRYL220、EBECRYL2220、KRM7735、KRM-8295(均為Daicel-Allnex公司製造)、Artresin UN-9000H、Artresin UN-9000A、Artresin UN-7100、Artresin UN-1255、Artresin UN-330、Artresin UN-3320HB、Artresin UN-1200TPK、Artresin SH-500B(均為根上工業公司製造)、U-2HA、U-2PHA、U-3HA、U-4HA、U-6H、U-6LPA、U-6HA、U-10H、U-15HA、U-122A、U-122P、U-108、U-108A、U-324A、U-340A、U-340P、U-1084A、U-2061BA、UA-340P、UA-4100、UA-4000、UA-4200、UA-4400、UA-5201P、UA-7100、UA-7200、UA-W2A(均為新中村化學工業公司製造)、AI-600、AH-600、AT-600、UA-101I、UA-101T、UA-306H、UA-306I、UA-306T(均為共榮社化學公司製造)等。 Examples of commercially available amine (meth) acrylates include M-1100, M-1200, M-1210, and M-1600 (all manufactured by Toa Kosei), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBCRYL5129, EBECRYL4842, EBECRYL210, EBCRYL20, EBCRYL6 , Artresin UN-9000H, Artresin UN-9000A, Artresin UN-7100, Artresin UN-1255, Artresin UN-330, Artresin UN-3320HB, Artresin UN-1200TPK, Artresin SH-500B (all manufactured by Kogen Industrial Corporation), U -2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U-122P, U-108, U-108A , U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA -7200, UA-W2A (all manufactured by Shin Nakamura Chemical Industry Co., Ltd.), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all Manufactured by Kyoeisha Chemical Co., Ltd.).
又，亦可適當地使用上述以外之其他自由基聚合性化合物。 Moreover, other radically polymerizable compounds other than the above may be used appropriately.
作為上述以外之自由基聚合性化合物，例如可列舉：N,N-二甲基(甲基)丙烯醯胺、N-(甲基)丙烯醯嗎福啉、N-羥乙基(甲基)丙烯醯胺、N,N-二乙基(甲基)丙烯醯胺、N-異丙基(甲基)丙烯醯胺、N,N-二甲胺基丙基(甲基)丙烯醯胺等(甲基)丙烯醯胺化合物、或苯乙烯、α-甲基苯乙烯、N-吡咯啶酮、N-乙烯基己內酯等乙烯系化合物等。 Examples of the radically polymerizable compound other than the above include N, N-dimethyl (meth) acrylamidonium, N- (meth) acrylamidomorpholine, and N-hydroxyethyl (methyl) Acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, etc. (Meth) acrylamide compounds, or vinyl compounds such as styrene, α-methylstyrene, N-pyrrolidone, and N-vinylcaprolactone.
就調整硬化性等觀點而言，上述自由基聚合性化合物較佳為含有單官能自由基聚合性化合物與多官能自由基聚合性化合物。於僅使用單官能自由基聚合性化合物之情形時，存在所獲得之光與溼氣硬化型樹脂組成物成為硬化性欠佳者之情況，於僅使用多官能自由基聚合性化合物之情形時，存在所獲得之光與溼氣硬化型樹脂組成物成為觸黏性欠佳者之情況。其中，更佳為將作為上述單官能自由基聚合性化合物之分子中具有氮 原子之化合物與作為上述多官能自由基聚合性化合物之(甲基)丙烯酸胺酯組合使用。又，上述多官能自由基聚合性化合物較佳為2官能或3官能，更佳為2官能。 From the viewpoint of adjusting the hardenability, it is preferable that the radical polymerizable compound contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound. When only a monofunctional radically polymerizable compound is used, there may be a case where the obtained light and moisture-curable resin composition becomes less hardenable. When only a multifunctional radically polymerizable compound is used, There may be cases where the obtained light and moisture-curable resin composition becomes poor in tackiness. Among them, it is more preferable that nitrogen is present in the molecule of the monofunctional radically polymerizable compound. Atomic compounds are used in combination with amine (meth) acrylate as the above-mentioned multifunctional radical polymerizable compound. The polyfunctional radically polymerizable compound is preferably difunctional or trifunctional, and more preferably difunctional.
於上述自由基聚合性化合物含有上述單官能自由基聚合性化合物與上述多官能自由基聚合性化合物之情形時，上述多官能自由基聚合性化合物之含量相對於上述單官能自由基聚合性化合物與上述多官能自由基聚合性化合物之合計100重量份，較佳之下限為2重量份，較佳之上限為30重量份。若上述多官能自由基聚合性化合物之含量未達2重量份，則存在所獲得之光與溼氣硬化型樹脂組成物成為硬化性欠佳者之情況。若上述多官能自由基聚合性化合物之含量超過30重量份，則存在所獲得之光與溼氣硬化型樹脂組成物成為觸黏性欠佳者之情況。上述多官能自由基聚合性化合物之含量之更佳之下限為5重量份，更佳之上限為20重量份。 When the said radically polymerizable compound contains the said monofunctional radically polymerizable compound and the said polyfunctional radically polymerizable compound, content of the said polyfunctional radically polymerizable compound with respect to the said monofunctional radically polymerizable compound and The total of the above-mentioned polyfunctional radical polymerizable compound is 100 parts by weight, with a preferred lower limit of 2 parts by weight and a preferred upper limit of 30 parts by weight. If the content of the above-mentioned polyfunctional radical polymerizable compound is less than 2 parts by weight, the obtained light and moisture-curable resin composition may be inferior in curability. When the content of the polyfunctional radically polymerizable compound exceeds 30 parts by weight, the obtained light and moisture-curable resin composition may become poor in tackiness. A more preferable lower limit of the content of the polyfunctional radical polymerizable compound is 5 parts by weight, and a more preferable upper limit is 20 parts by weight.
本發明之光與溼氣硬化型樹脂組成物含有溼氣硬化型胺酯樹脂。 The light and moisture-curable resin composition of the present invention contains a moisture-curable urethane resin.
上述溼氣硬化型胺酯樹脂之分子內之異氰酸酯基會與空氣中或被接著體中之水分產生反應而硬化。又，與使用具有交聯性矽烷基之化合物等作為溼氣硬化成分之情形相比，所獲得之光與溼氣硬化型樹脂組成物成為速硬化性優異者。 The isocyanate group in the molecule of the moisture-curable urethane resin reacts with moisture in the air or the adherend and hardens. Moreover, compared with the case where the compound etc. which have a crosslinkable silane group are used as a moisture hardening component, the obtained light and moisture hardening-type resin composition becomes the one excellent in rapid hardening property.
上述溼氣硬化型胺酯樹脂較佳為具有異氰酸酯基，1分子中既可僅具有1個異氰酸酯基，亦可具有2個以上。其中，較佳為於兩末端具有異氰酸酯基之胺酯預聚物。 The moisture-curable urethane resin preferably has an isocyanate group, and may have only one isocyanate group in one molecule, or may have two or more. Among these, an amine ester prepolymer having an isocyanate group at both ends is preferred.
上述胺酯預聚物可藉由使1分子中具有2個以上之羥基的多元醇化合物與1分子中具有2個以上之異氰酸酯基的聚異氰酸酯化合物反應而獲得。 The amine ester prepolymer can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule and a polyisocyanate compound having two or more isocyanate groups in one molecule.
上述多元醇化合物與聚異氰酸酯化合物之反應通常係於以多元醇化合物中之羥基(OH)與聚異氰酸酯化合物中之異氰酸酯基(NCO) 之莫耳比計[NCO]/[OH]=2.0~2.5之範圍內進行。 The reaction between the polyol compound and the polyisocyanate compound is usually based on the hydroxyl group (OH) in the polyol compound and the isocyanate group (NCO) in the polyisocyanate compound. Molar ratio [NCO] / [OH] = 2.0 ~ 2.5.
作為上述多元醇化合物，可使用聚胺酯之製造中通常所使用之公知之多元醇化合物，例如可列舉聚酯多元醇、聚醚多元醇、聚伸烷基多元醇、聚碳酸酯多元醇等。該等多元醇化合物既可單獨使用，亦可組合2種以上而使用。 As the polyol compound, known polyol compounds generally used in the production of polyurethanes can be used, and examples thereof include polyester polyols, polyether polyols, polyalkylene polyols, and polycarbonate polyols. These polyol compounds may be used alone or in combination of two or more kinds.
作為上述聚酯多元醇，例如可列舉藉由多元羧酸與多元醇之反應而獲得之聚酯多元醇、或使ε-己內酯開環聚合而獲得之聚-ε-己內酯多元醇等。 Examples of the polyester polyol include a polyester polyol obtained by reacting a polycarboxylic acid and a polyol, or a poly-ε-caprolactone polyol obtained by ring-opening polymerization of ε-caprolactone. Wait.
作為成為上述聚酯多元醇之原料之上述多元羧酸，例如可列舉：對苯二甲酸、間苯二甲酸、1,5-萘二甲酸、2,6-萘二甲酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十亞甲基二羧酸、十二亞甲基二羧酸等。 Examples of the polycarboxylic acid used as a raw material of the polyester polyol include terephthalic acid, isophthalic acid, 1,5-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, succinic acid, and glutaric acid. Acids, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, dodecamethylene dicarboxylic acid, and the like.
作為成為上述聚酯多元醇之原料之上述多元醇，例如可列舉：乙二醇、丙二醇、1,3-丙二醇、1,4-丁二醇、新戊二醇、1,5-戊二醇、1,6-己二醇、二乙二醇、環己二醇等。 Examples of the polyol that serves as a raw material for the polyester polyol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, and 1,5-pentanediol. , 1,6-hexanediol, diethylene glycol, cyclohexanediol and the like.
作為上述聚醚多元醇，例如可列舉：乙二醇、丙二醇、四氫呋喃、3-甲基四氫呋喃之開環聚合物、及該等或其衍生物之無規共聚物或嵌段共聚物、或雙酚型之聚氧伸烷基改質體等。 Examples of the polyether polyol include ethylene glycol, propylene glycol, tetrahydrofuran, ring-opening polymers of 3-methyltetrahydrofuran, and random or block copolymers of these or their derivatives, or Polyoxyalkylene modified body of phenol type and the like.
上述雙酚型之聚氧伸烷基改質體係使雙酚型分子骨架之活性氫部分與環氧烷(例如，環氧乙烷、環氧丙烷、環氧丁烷、環氧異丁烷等)進行加成反應而獲得之聚醚多元醇，既可為無規共聚物，亦可為嵌段共聚物。 The above-mentioned bisphenol-type polyoxyalkylene modification system enables the active hydrogen portion of the bisphenol-type molecular skeleton and alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc. The polyether polyol obtained by the addition reaction may be either a random copolymer or a block copolymer.
上述雙酚型之聚氧伸烷基改質體較佳為於雙酚型分子骨架之兩末端加成有1種或2種以上之環氧烷。作為雙酚型，並無特別限定，可列舉A型、F型、S型等，較佳為雙酚A型。 The bisphenol-type polyoxyalkylene modified body is preferably one or two or more kinds of alkylene oxides added to both ends of the bisphenol-type molecular skeleton. The bisphenol type is not particularly limited, and examples thereof include A type, F type, and S type, and a bisphenol A type is preferred.
作為上述聚伸烷基多元醇，例如可列舉聚丁二烯多元醇、氫化聚丁二烯多元醇、氫化聚異戊二烯多元醇等。 Examples of the polyalkylene polyol include polybutadiene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.
作為上述聚碳酸酯多元醇，例如可列舉聚六亞甲基碳酸酯多元醇、聚環己烷二亞甲基碳酸酯多元醇等。 Examples of the polycarbonate polyol include polyhexamethylene carbonate polyol, polycyclohexane dimethylene carbonate polyol, and the like.
作為上述聚異氰酸酯化合物，例如可列舉：二苯基甲烷二異氰酸酯、二苯基甲烷二異氰酸酯之液狀改質物、聚合MDI(甲烷二異氰酸酯)、甲苯二異氰酸酯、萘-1,5-二異氰酸酯等。其中，就蒸氣壓或毒性較低之方面、處理容易性之方面而言，較佳為二苯基甲烷二異氰酸酯及其改質物。上述聚異氰酸酯化合物既可單獨使用，亦可組合2種以上而使用。 Examples of the polyisocyanate compound include liquid improvements of diphenylmethane diisocyanate, diphenylmethane diisocyanate, polymerized MDI (methane diisocyanate), toluene diisocyanate, naphthalene-1,5-diisocyanate, and the like. . Among these, diphenylmethane diisocyanate and a modified product thereof are preferred in terms of low vapor pressure or toxicity and ease of handling. These polyisocyanate compounds may be used alone or in combination of two or more kinds.
又，上述溼氣硬化型胺酯樹脂較佳為使用具有下述式(1)所表示之結構之多元醇化合物而獲得者。藉由使用具有下述式(1)所表示之結構之多元醇化合物，可獲得接著性優異之組成物、或柔軟且伸長性較佳之硬化物，成為與上述自由基聚合性化合物之相溶性優異者。 The moisture-curable urethane resin is preferably obtained by using a polyol compound having a structure represented by the following formula (1). By using a polyhydric alcohol compound having a structure represented by the following formula (1), a composition having excellent adhesion or a hardened material having good flexibility and elongation can be obtained, and it has excellent compatibility with the above radical polymerizable compound. By.
其中，較佳為使用由丙二醇、或四氫呋喃(THF)化合物之開環聚合化合物、或具有甲基等取代基之四氫呋喃化合物之開環聚合化合物構成的聚醚多元醇。 Among them, a polyether polyol composed of propylene glycol, a ring-opening polymerization compound of a tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group is preferably used.
式(1)中，R表示氫、甲基、或乙基，n表示1~10之整數，L表示0~5之整數，m表示1~500之整數。n較佳為1~5，L較佳為0~4，m較佳為50~200。 In formula (1), R represents hydrogen, methyl, or ethyl, n represents an integer of 1 to 10, L represents an integer of 0 to 5, and m represents an integer of 1 to 500. n is preferably 1 to 5, L is preferably 0 to 4, and m is preferably 50 to 200.
再者，所謂L為0之情形，意指與R鍵結之碳直接與氧鍵結之情形。 The case where L is 0 means a case where the carbon bonded to R is directly bonded to oxygen.
進而，上述溼氣硬化型胺酯樹脂亦可具有自由基聚合性官能基。 Further, the moisture-curable urethane resin may have a radical polymerizable functional group.
作為上述溼氣硬化型胺酯樹脂亦可具有之自由基聚合性官能基，較佳為具有不飽和雙鍵之基，尤其就反應性之方面而言，更佳為(甲基)丙烯醯基。 As the radically polymerizable functional group that the moisture-curable amine ester resin may also have, a group having an unsaturated double bond is preferable, and in particular, a (meth) acrylfluorenyl group is more preferable in terms of reactivity. .
再者，具有自由基聚合性官能基之溼氣硬化型胺酯樹脂不包括於自由基聚合性化合物而作為溼氣硬化型胺酯樹脂處理。 The moisture-curable urethane resin having a radical polymerizable functional group is not included in the radical-polymerizable compound and is treated as a moisture-curable urethane resin.
上述溼氣硬化型胺酯樹脂之重量平均分子量之較佳之下限為800，較佳之上限為1萬。若上述溼氣硬化型胺酯樹脂之重量平均分子量未達800，則有交聯密度變高，柔軟性受損之情況。若上述溼氣硬化型胺酯樹脂之重量平均分子量超過1萬，則有所獲得之光與溼氣硬化型樹脂組成物成為塗佈性欠佳者之情況。上述溼氣硬化型胺酯樹脂之重量平均分子量之更佳之下限為2000，更佳之上限為8000，進而較佳之下限為3000，進而較佳之上限為6000。 A preferable lower limit of the weight-average molecular weight of the moisture-curable amine ester resin is 800, and a preferable upper limit is 10,000. If the weight-average molecular weight of the moisture-curable amine ester resin is less than 800, the cross-linking density may be increased, and flexibility may be impaired. If the weight-average molecular weight of the moisture-curable amine ester resin is more than 10,000, the obtained light and moisture-curable resin composition may become poor in coating properties. A more preferable lower limit of the weight-average molecular weight of the moisture-curable amine ester resin is 2000, a more preferable upper limit is 8000, a more preferable lower limit is 3000, and a more preferable upper limit is 6000.
再者，於本說明書中，上述重量平均分子量係利用凝膠滲透層析儀(GPC)進行測定，並藉由聚苯乙烯換算而求出之值。作為利用GPC測定藉由聚苯乙烯換算所得之重量平均分子量時之管柱，例如可列舉Shodex LF-804(昭和電工公司製造)等。又，作為GPC中使用之溶劑，可列舉四氫呋喃等。 In addition, in this specification, the said weight average molecular weight is a value measured by gel permeation chromatography (GPC), and calculated | required by polystyrene conversion. Examples of the column for measuring the weight-average molecular weight by polystyrene conversion by GPC include Shodex LF-804 (manufactured by Showa Denko). Examples of the solvent used in GPC include tetrahydrofuran.
上述溼氣硬化型胺酯樹脂之含量相對於上述自由基聚合性化合物與上述溼氣硬化型胺酯樹脂之合計100重量份，較佳之下限為20重量份，較佳之上限為90重量份。若上述溼氣硬化型胺酯樹脂之含量未達20重量份，則有所獲得之光與溼氣硬化型樹脂組成物成為溼氣硬化性欠佳者之情況。若上述溼氣硬化型胺酯樹脂之含量超過90重量份，則有所獲得之光與溼氣硬化型樹脂組成物成為光硬化性欠佳者之情況。上述溼氣硬化型胺酯樹脂之含量之更佳之下限為30重量份，更佳之上限為75重量份，進而較佳之下限為41重量份，進而較佳之上限為70重量份。 Content of the said moisture-hardening amine ester resin is 100 weight part with respect to the total of the said radically polymerizable compound and the said moisture-hardening amine ester resin, A preferable lower limit is 20 weight part, and a preferable upper limit is 90 weight part. If the content of the moisture-curable urethane resin is less than 20 parts by weight, the obtained light and moisture-curable resin composition may become a case where the moisture-curability is poor. When the content of the moisture-curable urethane resin is more than 90 parts by weight, the obtained light and moisture-curable resin composition may become poor in photo-curability. A more preferable lower limit of the content of the moisture-curable urethane resin is 30 parts by weight, a more preferable upper limit is 75 parts by weight, a more preferable lower limit is 41 parts by weight, and a more preferable upper limit is 70 parts by weight.
本發明之光與溼氣硬化型樹脂組成物含有光自由基聚合起 始劑。 The light and moisture-curable resin composition of the present invention contains photo-radical polymerization Starting agent.
作為上述光自由基聚合起始劑，例如可列舉二苯甲酮系化合物、苯乙酮系化合物、醯基氧化膦系化合物、二茂鈦系化合物、肟酯系化合物、安息香醚系化合物、9-氧硫等。 Examples of the photoradical polymerization initiator include benzophenone-based compounds, acetophenone-based compounds, fluorenylphosphine oxide-based compounds, titanocene-based compounds, oxime ester-based compounds, benzoin-ether-based compounds, 9 -Oxysulfur Wait.
作為上述光自由基聚合起始劑中之市售者，例如可列舉：IRGACURE184、IRGACURE369、IRGACURE379、IRGACURE651、IRGACURE784、IRGACURE819、IRGACURE907、IRGACURE2959、IRGACUREOXE01、Lucirin TPO(均為BASF Japan公司製造)、安息香甲醚、安息香乙醚、安息香異丙醚(均為東京化成工業公司製造)等。 Examples of the commercially available photoradical polymerization initiator include IRGACURE184, IRGACURE369, IRGACURE379, IRGACURE651, IRGACURE784, IRGACURE819, IRGACURE907, IRGACURE2959, IRGACUREOXE01, Lucirin TPO (all manufactured by BASF Japan), and benzoin. Ether, benzoin ether, benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.), and the like.
上述光自由基聚合起始劑之含量相對於上述自由基聚合性化合物100重量份，較佳之下限為0.01重量份，較佳之上限為10重量份。若上述光自由基聚合起始劑之含量未達0.01重量份，則有無法使所獲得之光與溼氣硬化型樹脂組成物充分地光硬化之情況。若上述光自由基聚合起始劑之含量超過10重量份，則有所獲得之光與溼氣硬化型樹脂組成物之保存穩定性降低之情況。上述光自由基聚合起始劑之含量之更佳之下限為0.1重量份，更佳之上限為5重量份。 Content of the said photo-radical polymerization initiator is 100 weight part with respect to the said radically polymerizable compound, Preferably a minimum is 0.01 weight part, and a preferable upper limit is 10 weight part. If the content of the photo-radical polymerization initiator is less than 0.01 part by weight, the obtained light and moisture-curable resin composition may not be sufficiently light-hardened. When the content of the photo-radical polymerization initiator exceeds 10 parts by weight, the storage stability of the obtained light and moisture-curable resin composition may be reduced. A more preferable lower limit of the content of the photo-radical polymerization initiator is 0.1 part by weight, and a more preferable upper limit is 5 parts by weight.
本發明之光與溼氣硬化型樹脂組成物含有填充劑。藉由含有上述填充劑，本發明之光與溼氣硬化型樹脂組成物成為具有較佳之搖變性者，可充分地保持塗佈後之形狀。 The light and moisture-curable resin composition of the present invention contains a filler. By containing the above-mentioned filler, the light and moisture-curable resin composition of the present invention becomes a person having better shake properties and can sufficiently maintain the shape after coating.
上述填充劑之一次粒徑之較佳之下限為1nm，較佳之上限為50nm。若上述填充劑之一次粒徑未達1nm，則有所獲得之光與溼氣硬化型樹脂組成物成為塗佈性欠佳者之情況。若上述填充劑之一次粒徑超過50nm，則有所獲得之光與溼氣硬化型樹脂組成物成為塗佈後之形狀保持性欠佳者之情況。上述填充劑之一次粒徑之更佳之下限為5nm，更佳之上限為30nm，進而較佳之下限為10nm，進而較佳之上限為20nm。 The preferred lower limit of the primary particle diameter of the filler is 1 nm, and the preferred upper limit is 50 nm. If the primary particle diameter of the filler is less than 1 nm, the obtained light and moisture-curable resin composition may become poor in coating properties. If the primary particle diameter of the filler exceeds 50 nm, the obtained light and moisture-curable resin composition may become a poor shape-retaining property after coating. The lower limit of the primary particle size of the filler is more preferably 5 nm, the more preferable upper limit is 30 nm, the more preferable lower limit is 10 nm, and the more preferable upper limit is 20 nm.
再者，上述填充劑之一次粒徑可使用NICOMP 380ZLS(PARTICLE SIZING SYSTEMS公司製造)，使上述填充劑分散於溶劑(水、有機溶劑等)中而測定。 The primary particle diameter of the filler can be measured by using NICOMP 380ZLS (manufactured by PARTICLE SIZING SYSTEMS), dispersing the filler in a solvent (water, organic solvent, etc.).
又，上述填充劑有於本發明之光與溼氣硬化型樹脂組成物中以二次粒子(複數個一次粒子聚集而成者)之形式存在之情形，此種二次粒子之粒徑之較佳之下限為5nm，較佳之上限為500nm，更佳之下限為10nm，更佳之上限為100nm。上述填充劑之二次粒子之粒徑可藉由使用穿透式電子顯微鏡(TEM)觀察本發明之光與溼氣硬化型樹脂組成物或其硬化物而測定。 Moreover, the filler mentioned above may exist in the form of secondary particles (composed of a plurality of primary particles) in the light and moisture-curable resin composition of the present invention. The lower limit is preferably 5 nm, the upper limit is 500 nm, the lower limit is 10 nm, and the upper limit is 100 nm. The particle diameter of the secondary particles of the filler can be measured by observing the light and moisture-curable resin composition of the present invention or a cured product thereof using a transmission electron microscope (TEM).
作為上述填充劑，較佳為無機填充劑，例如可列舉：二氧化矽(silica)、滑石、氧化鈦、氧化鋅、碳酸鈣等。其中，就所獲得之光與溼氣硬化型樹脂組成物成為UV光穿透性優異者之方面而言，較佳為二氧化矽。該等填充劑既可單獨使用，亦可組合2種以上而使用。 The filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, and calcium carbonate. Among these, silicon dioxide is preferred in that the obtained light and moisture-curable resin composition is excellent in UV light transmission. These fillers may be used alone or in combination of two or more.
上述填充劑較佳為經實施疏水性表面處理。藉由上述疏水性表面處理，所獲得之光與溼氣硬化型樹脂組成物成為塗佈後之形狀保持性更優異者。 The filler is preferably subjected to a hydrophobic surface treatment. By the above-mentioned hydrophobic surface treatment, the obtained light and moisture-curable resin composition becomes more excellent in shape retention after coating.
作為上述疏水性表面處理，可列舉矽烷化處理、烷化處理、環氧化處理等。其中，就提高形狀保持性之效果優異之方面而言，較佳為矽烷化處理，更佳為三甲基矽烷化處理。 Examples of the hydrophobic surface treatment include a silylation treatment, an alkylation treatment, and an epoxidation treatment. Among them, in terms of the effect of improving the shape retention property, a silylation treatment is preferred, and a trimethylsilanization treatment is more preferred.
作為對上述填充劑進行疏水性表面處理之方法，例如可列舉使用矽烷偶合劑等表面處理劑對填充劑之表面進行處理之方法等。 Examples of the method for the hydrophobic surface treatment of the filler include a method of treating the surface of the filler with a surface treatment agent such as a silane coupling agent.
具體而言，例如，經上述三甲基矽烷化處理之二氧化矽例如可藉由如下方法等而製作：利用溶膠凝膠法等方法合成二氧化矽，於使二氧化矽流動之狀態下霧狀噴出六甲基二矽氮烷之方法；或於醇、甲苯等有機溶劑中添加二氧化矽，進而添加六甲基二矽氮烷及水，其後利用蒸發器使水與有 機溶劑蒸發乾燥之方法。 Specifically, for example, the above-mentioned trimethylsilanized silicon dioxide can be produced by, for example, the following method: the silicon dioxide is synthesized by a method such as a sol-gel method, and the silicon dioxide is fogged in a state where the silicon dioxide flows A method of spraying hexamethyldisilazane; or adding silicon dioxide to an organic solvent such as alcohol and toluene, and then adding hexamethyldisilazane and water, and then using an evaporator to make water and Organic solvent evaporation method.
上述填充劑之含量相對於上述自由基聚合性化合物與上述溼氣硬化型胺酯樹脂之合計100重量份，較佳之下限為1重量份，較佳之上限為20重量份。若上述填充劑之含量未達1重量份，則有所獲得之光與溼氣硬化型樹脂組成物成為塗佈後之形狀保持性欠佳者之情形。若上述填充劑之含量超過20重量份，則有所獲得之光與溼氣硬化型樹脂組成物成為塗佈性欠佳者之情形。上述填充劑之含量之更佳之下限為2重量份，更佳之上限為15重量份，進而較佳之下限為3重量份，進而較佳之上限為10重量份，特佳之下限為4重量份。 Content of the said filler is 100 weight part with respect to the total of the said radically polymerizable compound and the said moisture hardening type urethane resin, Preferably a minimum is 1 weight part, and a preferable upper limit is 20 weight part. If the content of the filler is less than 1 part by weight, the obtained light and moisture-curable resin composition may become the one having poor shape retention after coating. When the content of the filler is more than 20 parts by weight, the obtained light and moisture-curable resin composition may become poor in coating properties. A more preferred lower limit of the content of the filler is 2 parts by weight, a more preferred upper limit is 15 parts by weight, a further preferred lower limit is 3 parts by weight, a further preferred upper limit is 10 parts by weight, and a particularly preferred lower limit is 4 parts by weight.
本發明之光與溼氣硬化型樹脂組成物較佳為含有具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物。上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物與水分之反應性較高，且具有防止保存時之溼氣硬化型胺酯樹脂與水分之反應的功效。再者，具有胺酯鍵與異氰酸酯基之化合物係作為上述溼氣硬化型胺酯樹脂處理。 The light and moisture-curable resin composition of the present invention preferably contains a compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group. The compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group has high reactivity with moisture and prevents moisture hardening during storage. Efficacy of the amine ester resin in response to moisture. The compound having an amine ester bond and an isocyanate group is treated as the moisture-curable amine ester resin.
上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物必須於系統中移動以與水分迅速地反應，因此，較佳為分子量較小，尤其於具有異氰酸酯基或異硫氰酸酯基之化合物之情形時，分子量之較佳之上限為500，更佳之上限為300。又，就加快與水分之反應速度而有效地去除水分之觀點而言，較佳為包含具有芳香族環之異氰酸酯基、或具有芳香族環之異硫氰酸酯基之化合物。再者，對於具有碳二醯亞胺基之化合物，並無特別限制。又，未與水分反應之具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物有助於溼氣硬化型胺酯樹脂之硬化，且交聯密度提高，藉此，所獲得之光與溼氣硬化型樹脂組成物之硬化物成為接著性優異者。 The compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group must move in the system to react quickly with moisture, and therefore, it is preferable The molecular weight is relatively small, especially in the case of a compound having an isocyanate group or an isothiocyanate group. A preferable upper limit of the molecular weight is 500, and a more preferable upper limit is 300. From the viewpoint of efficiently removing moisture by accelerating the reaction rate with moisture, a compound containing an isocyanate group having an aromatic ring or an isothiocyanate group having an aromatic ring is preferred. The compound having a carbodiimide group is not particularly limited. In addition, a compound having at least one type selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group that does not react with moisture contributes to the moisture-curable urethane resin. It is hardened and the crosslinking density is increased, whereby the cured product of the light and moisture-curable resin composition obtained is excellent in adhesion.
上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物既可為單官能，亦可為多官能，但就對水分具有適度之反應性之方面而言，較佳為2官能。 The compound having at least one kind of group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group may be monofunctional or polyfunctional, but it has a property of water In terms of moderate reactivity, difunctional is preferred.
再者，上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物為化學性地將水分去除者，亦可於調配本發明之光與溼氣硬化型樹脂組成物所使用之各材料之前，預先視需要對各材料進行物理性之處理(藉由如沸石之水分吸附劑去除水分)。 In addition, the compound having at least one type selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group is one that chemically removes water. Before inventing the materials used in the light and moisture-curable resin composition, each material is physically treated in advance (removal of water by a moisture adsorbent such as zeolite) as necessary.
上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物中，就提高交聯密度，使所獲得之光與溼氣硬化型樹脂組成物之硬化物為接著性優異者的效果優異之方面而言，較佳為具有異氰酸酯基之化合物。 The compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group increases the crosslinking density and hardens the obtained light and moisture. The hardened | cured material of the type resin composition is a compound which has an isocyanate group from the point which is excellent in the effect of the outstanding adhesiveness.
上述具有異氰酸酯基之化合物既可為與成為上述溼氣硬化型胺酯樹脂之原料之聚異氰酸酯化合物相同之化合物，亦可不同。 The compound having an isocyanate group may be the same compound as the polyisocyanate compound used as a raw material of the moisture-curable urethane resin, or may be different.
作為上述具有異氰酸酯基之化合物，具體而言，例如可列舉：異佛爾酮二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、六亞甲基二異氰酸酯、三甲基六亞甲基二異氰酸酯、二苯基甲烷-4,4'-二異氰酸酯(MDI)、氫化MDI、聚合MDI、1,5-萘二異氰酸酯(NDI)、降莰烷二異氰酸酯、聯甲苯胺二異氰酸酯、苯二甲基二異氰酸酯(XDI)、氫化XDI、離胺酸二異氰酸酯、三苯甲烷三異氰酸酯、三(異氰酸酯基苯基)硫代磷酸酯、四甲基二甲苯二異氰酸酯、1,6,10-十一烷三異氰酸酯等。 Specific examples of the compound having an isocyanate group include isophorone diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, and trimethylhexaene. Methylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, 1,5-naphthalene diisocyanate (NDI), norbornane diisocyanate, ditoluidine diisocyanate , Xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) phosphorothioate, tetramethylxylene diisocyanate, 1,6, 10-undecane triisocyanate and the like.
又，作為具有異硫氰酸酯基之化合物，具體而言，例如可列舉：異硫氰酸苄酯、異硫氰酸苯酯、異硫氰酸4-苯基丁酯、異硫氰酸3-苯基丙酯等。 Specific examples of the compound having an isothiocyanate group include benzyl isothiocyanate, phenyl isothiocyanate, 4-phenylbutyl isothiocyanate, and isothiocyanate. 3-phenylpropyl ester and the like.
又，作為具有碳二醯亞胺基之化合物，具體而言，例如可列舉：N,N-二環己基碳二醯亞胺、N,N-二異丙基碳二醯亞胺、1-乙基-3-(3-二甲基胺基丙基)碳二醯亞胺鹽酸鹽、雙(2,6-二異丙基苯基)碳二醯亞胺等，作為市售者， 例如可列舉Carbodilite LA-1(日清紡公司製造)等。 Specific examples of the compound having a carbodiimide group include N, N-dicyclohexylcarbodiimide, N, N-diisopropylcarbodiimide, 1- As marketers, ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, bis (2,6-diisopropylphenyl) carbodiimide, etc. Examples include Carbodilite LA-1 (manufactured by Nisshinbo).
該等既可單獨使用，亦可組合2種以上而使用。 These may be used alone or in combination of two or more.
上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物之含量於本發明之光與溼氣硬化型樹脂組成物整體100重量份中，較佳之下限為0.05重量份，較佳之上限為10重量份。若上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物之含量未達0.05重量份，則有所獲得之光與溼氣硬化型樹脂組成物成為保存穩定性或接著性欠佳者之情況。若上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物之含量超過10重量份，則有溼氣硬化型胺酯樹脂之硬化時之交聯度過度上升，變得硬且脆之情況。上述具有選自由異氰酸酯基、異硫氰酸酯基、及碳二醯亞胺基所組成之群中之至少1種基的化合物之含量之更佳之下限為0.1重量份，更佳之上限為3.0重量份，進而較佳之下限為0.2重量份，進而較佳之上限為1.5重量份。 The content of the compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group is 100% of the light and moisture-curable resin composition of the present invention. Of the parts by weight, the preferred lower limit is 0.05 parts by weight, and the preferred upper limit is 10 parts by weight. If the content of the compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group is less than 0.05 parts by weight, the obtained light and humidity are obtained. The gas-curable resin composition may be a case in which storage stability or adhesion is poor. If the content of the compound having at least one type selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group exceeds 10 parts by weight, there is a moisture-curable amine ester resin. In the case of hardening, the degree of crosslinking is excessively increased, and becomes hard and brittle. The lower limit of the content of the compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group is 0.1 parts by weight, and a more preferable upper limit is 3.0 weight. The more preferable lower limit is 0.2 parts by weight, and the more preferable upper limit is 1.5 parts by weight.
本發明之光與溼氣硬化型樹脂組成物亦可含有遮光劑。藉由含有上述遮光劑，本發明之光與溼氣硬化型樹脂組成物成為遮光性優異者而可防止顯示元件之漏光。 The light and moisture-curable resin composition of the present invention may contain a light-shielding agent. By including the above-mentioned light-shielding agent, the light and moisture-curable resin composition of the present invention is excellent in light-shielding properties and can prevent light leakage from a display element.
再者，本說明書中，上述「遮光劑」意指具有使可見光區域之光不易穿透之能力之材料。 In addition, in the present specification, the "shielding agent" means a material having the ability to make light in the visible light region difficult to penetrate.
作為上述遮光劑，例如可列舉：氧化鐵、鈦黑、苯胺黑、花青黑、富勒烯、碳黑、樹脂被覆型碳黑等。 Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black.
又，上述遮光劑亦可不呈現黑色，只要為具有使可見光區域之光不易穿透之能力之材料即可，二氧化矽、滑石、鈦等作為填充劑所列舉之材料等亦包括於上述遮光劑。其中，較佳為鈦黑。 In addition, the above-mentioned light-shielding agent may not be black, as long as it is a material having the ability to make light in the visible light region difficult to penetrate. Materials such as silicon dioxide, talc, and titanium as fillers are also included in the above-mentioned light-shielding agent. . Among these, titanium black is preferred.
上述鈦黑為如下物質：與對於波長300~800nm之光之平均 穿透率相比，對於紫外線區域附近、尤其波長370~450nm之光之穿透率較高。 The above-mentioned titanium black is the following: average with respect to light with a wavelength of 300 to 800 nm Compared with the transmittance, it has a higher transmittance in the vicinity of the ultraviolet region, especially for light having a wavelength of 370 to 450 nm.
即，上述鈦黑為具有如下性質之遮光劑：一方面，藉由充分地遮蔽可見光區域之波長之光而對本發明之光與溼氣硬化型樹脂組成物賦予遮光性，另一方面，使紫外線區域附近之波長之光穿透。因此，藉由使用可利用上述鈦黑之穿透率較高之波長(370~450nm)之光開始反應者作為光自由基聚合起始劑，可進一步提高本發明之光與溼氣硬化型樹脂組成物之光硬化性。又，另一方面，作為本發明之光與溼氣硬化型樹脂組成物中所含有之遮光劑，較佳為絕緣性較高之物質，作為絕緣性較高之遮光劑，亦較佳為鈦黑。 That is, the above-mentioned titanium black is a light-shielding agent having the properties of providing light-shielding properties to the light and the moisture-curable resin composition of the present invention by sufficiently shielding light of a wavelength in the visible light region, and ultraviolet rays Light of wavelengths near the area penetrates. Therefore, the light and moisture-curable resin of the present invention can be further improved by using a light-starting polymerization initiator as a photo-radical polymerization initiator that can use the light with a higher wavelength (370 to 450 nm) of the above-mentioned titanium black to transmit light. Light-curing properties of the composition. On the other hand, as the light-shielding agent contained in the light-and-moisture-curable resin composition of the present invention, a material having high insulation properties is preferred, and as a light-shielding agent having high insulation properties, titanium is also preferred. black.
上述鈦黑之光學濃度(OD值)較佳為3以上，更佳為4以上。又，上述鈦黑之黑色度(L值)較佳為9以上，更佳為11以上。上述鈦黑之遮光性越高越佳，上述鈦黑之OD值並無較佳之上限，但通常為5以下。 The optical density (OD value) of the titanium black is preferably 3 or more, and more preferably 4 or more. The blackness (L value) of the titanium black is preferably 9 or more, and more preferably 11 or more. The higher the light-shielding property of the titanium black, the better. The OD value of the titanium black has no preferable upper limit, but it is usually 5 or less.
關於上述鈦黑，即便為未經表面處理者亦發揮充分之效果，但亦可使用表面經偶合劑等有機成分處理者、或表面由氧化矽、氧化鈦、氧化鍺、氧化鋁、氧化鋯、氧化鎂等無機成分被覆者等經表面處理之鈦黑。其中，經有機成分處理者就可進一步提高絕緣性之方面而言較佳。 Regarding the above-mentioned titanium black, it has sufficient effects even if it is not surface-treated, but it can also be treated with organic components such as a coupling agent on the surface, or silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconia, Surface treated titanium black, such as those coated with inorganic components such as magnesium oxide. Among them, those treated with an organic component are preferred in terms of further improving the insulation properties.
又，使用本發明之光與溼氣硬化型樹脂組成物而製造之顯示元件由於光與溼氣硬化型樹脂組成物具有充分之遮光性，故而成為無光之漏出而具有高對比度，且具有優異之圖像顯示品質者。 In addition, a display element manufactured using the light and moisture-curable resin composition of the present invention has sufficient light-shielding properties, so it has no leakage of light, has high contrast, and is excellent. The image display quality.
作為上述鈦黑中之市售者，例如可列舉12S、13M、13M-C、13R-N(均為Mitsubishi Material公司製造)、Tilack D(赤穂化成公司製造)等。 Examples of the marketer of the titanium black include 12S, 13M, 13M-C, 13R-N (all manufactured by Mitsubishi Material), and Tilack D (manufactured by Akagi Kasei).
上述鈦黑之比表面積之較佳之下限為5m2/g，較佳之上限為40m2/g，更佳之下限為10m2/g，更佳之上限為25m2/g。 The preferable lower limit of the specific surface area of the titanium black is 5 m 2 / g, the preferable upper limit is 40 m 2 / g, the more preferable lower limit is 10 m 2 / g, and the more preferable upper limit is 25 m 2 / g.
又，上述鈦黑之片電阻之較佳之下限於與樹脂混合之情形時(70%調配)為109Ω/□，更佳之下限為1011Ω/□。 In addition, the lower limit of the above-mentioned titanium black sheet resistance is limited to a case where it is mixed with a resin (70% blending) is 10 9 Ω / □, and a more preferable lower limit is 10 11 Ω / □.
於本發明之光與溼氣硬化型樹脂組成物中，上述遮光劑之一次粒徑根據用途適當選擇，為顯示元件之基板間之距離以下等，較佳之下限為30nm，較佳之上限為500nm。若上述遮光劑之一次粒徑未達30nm，則有所獲得之光與溼氣硬化型樹脂組成物之黏度或搖變性大幅增大，而作業性變差之情況。若上述遮光劑之一次粒徑超過500nm，則有所獲得之光與溼氣硬化型樹脂組成物中之遮光劑之分散性降低，而遮光性降低之情況。上述遮光劑之一次粒徑之更佳之下限為50nm，更佳之上限為200nm。 In the light and moisture-curable resin composition of the present invention, the primary particle diameter of the light-shielding agent is appropriately selected according to the application, and is equal to or less than the distance between the substrates of the display element. The lower limit is preferably 30 nm, and the upper limit is preferably 500 nm. If the primary particle diameter of the light-shielding agent is less than 30 nm, the viscosity or shake of the obtained light and moisture-curable resin composition may be greatly increased, and the workability may be deteriorated. If the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the obtained light and moisture-curable resin composition may decrease, and the light-shielding property may decrease. The lower limit of the primary particle size of the above-mentioned sunscreen is more preferably 50 nm, and the more preferable upper limit is 200 nm.
本發明之光與溼氣硬化型樹脂組成物整體中之上述遮光劑之含量並無特別限定，較佳之下限為0.05重量%，較佳之上限為10重量%。若上述遮光劑之含量未達0.05重量%，則有無法獲得足夠遮光性之情況。若上述遮光劑之含量超過10重量%，則有所獲得之光與溼氣硬化型樹脂組成物之對於基板等之接著性或硬化後之強度降低，或繪圖性降低之情況。上述遮光劑之含量之更佳之下限為0.1重量%，更佳之上限為2重量%，進而較佳之上限為1重量%。 The content of the above-mentioned light-shielding agent in the entire light and moisture-curable resin composition of the present invention is not particularly limited, and the preferred lower limit is 0.05% by weight, and the preferred upper limit is 10% by weight. If the content of the light-shielding agent is less than 0.05% by weight, sufficient light-shielding properties may not be obtained. When the content of the above-mentioned light-shielding agent exceeds 10% by weight, the adhesion of the obtained light and moisture-curable resin composition to the substrate or the strength after curing may be reduced, or the drawability may be reduced. A more preferable lower limit of the content of the above-mentioned sunscreen agent is 0.1% by weight, a more preferable upper limit is 2% by weight, and a more preferable upper limit is 1% by weight.
本發明之光與溼氣硬化型樹脂組成物亦可進而視需要含有著色劑、離子液體、溶劑、含金屬之粒子、反應性稀釋劑等添加劑。 The light and moisture-curable resin composition of the present invention may further contain additives such as a colorant, an ionic liquid, a solvent, metal-containing particles, and a reactive diluent, if necessary.
作為製造本發明之光與溼氣硬化型樹脂組成物之方法，例如可列舉使用均質分散機、均質混合機、萬能混合機、行星式混合機、捏合機、三輥研磨機等混合機，將自由基聚合性化合物、溼氣硬化型胺酯樹脂、光自由基聚合起始劑、填充劑、及視需要添加之添加劑混合之方法等。 Examples of the method for producing the light and moisture-curable resin composition of the present invention include using a homomixer, a homomixer, a universal mixer, a planetary mixer, a kneader, a three-roll mill, and the like. A method of mixing a radical polymerizable compound, a moisture-curable amine ester resin, a photoradical polymerization initiator, a filler, and an additive added as necessary.
本發明之光與溼氣硬化型樹脂組成物較佳為所含之水分量為100ppm以下。若上述水分量超過100ppm，則於保存中上述溼氣硬化型胺酯樹脂與水分容易反應，光與溼氣硬化型樹脂組成物成為保存穩定性欠 佳者。上述水分量更佳為80ppm以下。 The light and moisture-curable resin composition of the present invention preferably contains a water content of 100 ppm or less. When the moisture content exceeds 100 ppm, the moisture-curable amine ester resin and moisture easily react during storage, and the light and moisture-curable resin composition become poor in storage stability. The best. The water content is more preferably 80 ppm or less.
再者，上述水分量可利用卡費水分測定裝置進行測定。 The above-mentioned moisture content can be measured by a Kari moisture measuring device.
本發明之光與溼氣硬化型樹脂組成物之使用錐板型黏度計於25℃、1rpm之條件下測定出的黏度之較佳之下限為50Pa‧s，較佳之上限為500Pa‧s。若上述黏度未達50Pa‧s或超過500Pa‧s，則於將光與溼氣硬化型樹脂組成物用於電子零件用接著劑或顯示元件用接著劑之情形時，有塗佈於基板等被接著體時之作業性變差之情況。上述黏度之更佳之下限為80Pa‧s，更佳之上限為300Pa‧s，進而較佳之上限為200Pa‧s。 The lower limit of the viscosity of the light and moisture-curable resin composition of the present invention measured at 25 ° C and 1 rpm using a cone-plate viscosity meter is 50 Pa · s, and the preferred upper limit is 500 Pa · s. If the viscosity is less than 50Pa‧s or more than 500Pa‧s, when the light and moisture-curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements, it may be coated on a substrate or the like. Cases where workability is deteriorated when following up. The lower limit of the above viscosity is 80Pa‧s, the upper limit is 300Pa‧s, and the upper limit is 200Pa‧s.
本發明之光與溼氣硬化型樹脂組成物之搖變度之較佳之下限為1.3，較佳之上限為5.0。若上述搖變度未達1.3或超過5.0，則有於將光與溼氣硬化型樹脂組成物用於電子零件用接著劑或顯示元件用接著劑之情形時塗佈於基板等被接著體時之作業性變差之情況。上述搖變度之更佳之下限為1.5，更佳之上限為4.0。 A preferable lower limit of the shake degree of the light and moisture-curable resin composition of the present invention is 1.3, and a preferable upper limit is 5.0. When the degree of shake is less than 1.3 or more than 5.0, when the light and moisture-curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements, it may be applied to an adherend such as a substrate. When the workability is deteriorated. The lower limit of the above-mentioned shake degree is more preferably 1.5, and the more preferable upper limit is 4.0.
再者，於本說明書中，所謂上述搖變度，意指使用錐板型黏度計於25℃、1rpm之條件下測定出之黏度除以使用錐板型黏度計於25℃、10rpm之條件下測定出之黏度而得之值。 In addition, in the present specification, the above-mentioned shake degree means the viscosity measured under the conditions of 25 ° C. and 1 rpm using a cone-plate type viscometer divided by 25 ° C. and 10 rpm using a cone-plate type viscometer. The value obtained by measuring the viscosity.
本發明之光與溼氣硬化型樹脂組成物較佳為硬化後之1mm厚之硬化物之光學濃度(OD值)為1以上。若上述OD值未達1，則有遮光性變得不足，於用於顯示元件之情形時產生光之漏出，無法獲得高對比度之情況。上述OD值更佳為1.5以上。 The light and moisture-curable resin composition of the present invention preferably has an optical density (OD value) of 1 or more of the cured material having a thickness of 1 mm after curing. If the OD value is less than 1, the light-shielding property may be insufficient, and light leakage may occur when used for a display element, and high contrast may not be obtained. The above OD value is more preferably 1.5 or more.
雖然上述OD值越高越佳，但若為提高上述OD值而過度調配大量遮光劑，則會產生因增黏而導致之作業性降低等，因此，為取得與遮光劑之調配量之平衡，上述硬化體之OD值之較佳之上限為4。 Although the higher the OD value, the better, but if a large amount of sunscreen is excessively formulated to increase the OD value, the workability will be reduced due to thickening. Therefore, in order to achieve a balance with the amount of sunscreen, A preferable upper limit of the OD value of the hardened body is 4.
再者，上述光與溼氣硬化型樹脂組成物之硬化後之OD值可使用光學濃度計進行測定。 The OD value of the light and moisture-curable resin composition after curing can be measured using an optical densitometer.
本發明之光與溼氣硬化型樹脂組成物之硬化物之於25℃之拉伸彈性模數之較佳之下限為0.5kgf/cm2，較佳之上限為6kgf/cm2。若上述拉伸彈性模數未達0.5kgf/cm2，則有過於柔軟，凝集力較弱，而接著力變低之情況。若上述拉伸彈性模數超過6kgf/cm2，則有柔軟性受損之情況。上述拉伸彈性模數之更佳之下限為1kgf/cm2，更佳之上限為4kgf/cm2。 The lower limit of the tensile elastic modulus of the cured product of the light and moisture-curable resin composition of the present invention at 25 ° C is preferably 0.5 kgf / cm 2 , and the preferable upper limit is 6 kgf / cm 2 . If the above-mentioned tensile elastic modulus is less than 0.5 kgf / cm 2 , it may be too soft, the cohesive force may be weak, and the adhesion force may become low. When the tensile elastic modulus exceeds 6 kgf / cm 2 , the flexibility may be impaired. A more preferable lower limit of the tensile elastic modulus is 1 kgf / cm 2 , and a more preferable upper limit is 4 kgf / cm 2 .
再者，於本說明書中，上述「拉伸彈性模數」意指使用拉伸試驗機(例如，島津製作所公司製造，「EZ-Graph」)，以10mm/min之速度拉伸硬化物，測定伸長50%時之力而得之值。 In addition, in the present specification, the "tensile elastic modulus" means a tensile tester (for example, "EZ-Graph" manufactured by Shimadzu Corporation) is used to measure a hardened product at a speed of 10 mm / min, and the measurement is performed. Value obtained by force at 50% elongation.
本發明之光與溼氣硬化型樹脂組成物可尤佳地用作電子零件用接著劑或顯示元件用接著劑。又，使用本發明之光與溼氣硬化型樹脂組成物而成之電子零件用接著劑、及使用本發明之光與溼氣硬化型樹脂組成物而成之顯示元件用接著劑亦分別為本發明之一。 The light and moisture-curable resin composition of the present invention is particularly useful as an adhesive for electronic parts or an adhesive for display elements. The adhesive for electronic parts using the light and moisture curing resin composition of the present invention, and the adhesive for display elements using the light and moisture curing resin composition of the present invention are also respectively Invention one.
根據本發明，可提供一種形狀保持性、接著性、速硬化性、及塗佈性優異之光與溼氣硬化型樹脂組成物。又，根據本發明，可提供一種使用該光與溼氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 According to the present invention, it is possible to provide a light and moisture-curable resin composition excellent in shape retention, adhesion, rapid curing, and coatability. Furthermore, according to the present invention, it is possible to provide an adhesive for electronic parts and an adhesive for display elements using the light and moisture-curable resin composition.
1‧‧‧載玻片 1‧‧‧ slide
2‧‧‧光與溼氣硬化型樹脂組成物 2‧‧‧Light and moisture hardening resin composition
圖1(a)係表示自上方觀察接著性評價用樣品之情形時之模式圖，(b)係表示自側面觀察接著性評價用樣品之情形時之模式圖。 FIG. 1 (a) is a schematic diagram when the sample for adhesion evaluation is viewed from above, and (b) is a schematic diagram when the sample for adhesion evaluation is viewed from the side.
以下，揭示實施例而更詳細地說明本發明，但本發明並不僅限定於該等實施例。 Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
(合成例1(胺酯預聚物A之製作)) (Synthesis example 1 (production of amine ester prepolymer A))
將作為多元醇之100重量份之聚四亞甲基醚二醇(三菱化學公司製造，「PTMG-2000」)、與0.01重量份之二丁基二月桂酸錫加入500mL容量之可分離式燒瓶中，於真空下(20mmHg以下)且以100℃攪拌30分鐘進行混合。其後，設為常壓，加入作為二異氰酸酯之26.5重量份之Pure MDI(日曹商事公司製造)，於80℃攪拌3小時而使其等反應，獲得胺酯預聚物A(重量平均分子量2700)。 As a polyol, 100 parts by weight of polytetramethylene ether glycol (manufactured by Mitsubishi Chemical Corporation, "PTMG-2000") and 0.01 part by weight of dibutyltin dilaurate were added to a separable flask having a capacity of 500 mL. The mixture was mixed under vacuum (20 mmHg or less) and stirred at 100 ° C for 30 minutes. Then, it was set to normal pressure, 26.5 parts by weight of Pure MDI (manufactured by Nissho Corporation) was added as a diisocyanate, and the mixture was stirred at 80 ° C. for 3 hours to be reacted to obtain an amine ester prepolymer A (weight average molecular weight). 2700).
(合成例2(胺酯預聚物B之製作)) (Synthesis example 2 (production of amine ester prepolymer B))
將作為多元醇之100重量份之EXCENOL 2020(旭硝子公司製造)、及0.01重量份之二丁基二月桂酸錫加入500mL容量之可分離式燒瓶中，於真空下(20mmHg以下)且以100℃攪拌30分鐘進行混合。其後，設為常壓，加入作為二異氰酸酯之26.5重量份之Pure MDI(日曹商事公司製造)，於80℃攪拌3小時而使其等反應，獲得胺酯預聚物B(重量平均分子量2900)。 100 parts by weight of EXCENOL 2020 (manufactured by Asahi Glass Co., Ltd.) as a polyol, and 0.01 parts by weight of dibutyltin dilaurate were added to a separable flask having a capacity of 500 mL, under vacuum (20 mmHg or less) at 100 ° C. Stir for 30 minutes to mix. Thereafter, it was set to normal pressure, 26.5 parts by weight of Pure MDI (manufactured by Nissho Corporation) was added as a diisocyanate, and the mixture was stirred at 80 ° C. for 3 hours to be reacted to obtain an amine ester prepolymer B (weight average molecular weight). 2900).
(合成例3(胺酯預聚物C之製作)) (Synthesis example 3 (production of amine ester prepolymer C))
於加入有以與合成例1同樣之方法獲得之胺酯預聚物A之反應容器中，添加甲基丙烯酸羥基乙酯1.3重量份、及作為聚合抑制劑之N-亞硝基苯基羥胺鋁鹽(和光純藥工業公司製造，「Q-1301」)0.14重量份，於氮氣流下且以80℃攪拌混合1小時，獲得於分子末端具有異氰酸酯基及甲基丙烯醯基之胺酯預聚物C(重量平均分子量3100)。 In a reaction vessel containing the amine ester prepolymer A obtained in the same manner as in Synthesis Example 1, 1.3 parts by weight of hydroxyethyl methacrylate and N-nitrosophenylhydroxylamine as a polymerization inhibitor were added. 0.14 parts by weight of salt (manufactured by Wako Pure Chemical Industries, Ltd., "Q-1301"), stirred and mixed at 80 ° C for 1 hour under a nitrogen stream to obtain an amine ester prepolymer having an isocyanate group and a methacrylfluorene group at the molecular ends C (weight average molecular weight 3100).
(合成例4(胺酯預聚物D之製作)) (Synthesis example 4 (production of amine ester prepolymer D))
將作為多元醇之100重量份之Kuraray Polyol P-5010(Kuraray公司製造)、及0.01重量份之二丁基二月桂酸錫加入500mL容量之可分離式燒瓶中，於真空下(20mmHg以下)且以100℃攪拌30分鐘進行混合。其後，設為常壓，加入作為二異氰酸酯之10.5重量份之Pure MDI(日曹商事公司製造)，於80℃攪拌3小時而使其等反應，獲得胺酯預聚物D(重量平均分子量5700)。 100 parts by weight of Kuraray Polyol P-5010 (manufactured by Kuraray) as a polyol, and 0.01 part by weight of dibutyltin dilaurate were added to a separable flask having a capacity of 500 mL, under vacuum (20 mmHg or less) and The mixture was stirred at 100 ° C for 30 minutes and mixed. Thereafter, it was set to normal pressure, and 10.5 parts by weight of Pure MDI (manufactured by Nissho Corporation) was added as a diisocyanate, and the mixture was stirred at 80 ° C. for 3 hours to be reacted to obtain an amine ester prepolymer D (weight average molecular weight). 5700).
(實施例1~23、比較例1~4) (Examples 1 to 23, Comparative Examples 1 to 4)
依照表1~3所記載之調配比，將各材料利用行星式攪拌裝置(Thinky公司製造，「去泡攪拌太郎」)進行攪拌後，利用陶瓷三輥研磨機均一地進行混合而獲得實施例1~23、比較例1~4之光與溼氣硬化型樹脂組成物。 In accordance with the mixing ratios described in Tables 1 to 3, each material was stirred with a planetary stirring device (manufactured by Thinky, "defoaming stirring Taro"), and then uniformly mixed with a ceramic three-roll mill to obtain Example 1. ~ 23. The light and moisture-curable resin compositions of Comparative Examples 1 to 4.
再者，表中之「胺酯預聚物A」係合成例1中所記載之於兩末端具有異氰酸酯基之胺酯預聚物，「胺酯預聚物B」係合成例2中所記載之於兩末端具有異氰酸酯基之胺酯預聚物，「胺酯預聚物C」係合成例3中所記載之於分子末端具有異氰酸酯基及甲基丙烯醯基之胺酯預聚物，「胺酯預聚物D」係合成例4中所記載之於兩末端具有異氰酸酯基之胺酯預聚物。 The "amine ester prepolymer A" in the table is an amine ester prepolymer having isocyanate groups at both ends described in Synthesis Example 1, and the "amine ester prepolymer B" is described in Synthesis Example 2. For an amine ester prepolymer having an isocyanate group at both ends, the "amine ester prepolymer C" is an amine ester prepolymer having an isocyanate group and a methacryl group at the molecular end described in Synthesis Example 3, " The amine ester prepolymer D "is an amine ester prepolymer having isocyanate groups at both ends described in Synthesis Example 4.
<評價> <Evaluation>
對實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物進行以下評價。將結果示於表1~3。 The following evaluations were performed on each of the light and moisture-curable resin compositions obtained in the examples and comparative examples. The results are shown in Tables 1 to 3.
(塗佈性(細孔通過性)) (Coatability (pore penetration))
於口徑4cm之過濾裝置中鋪設150目之濾紙，以0.2MPa之壓力對實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物30g進行加壓過濾，評估其通過時間。將通過所需之時間未達20秒之情形評價為「◎」，將20秒以上且未達30秒之情形評價為「○」，將通過所需之時間為30秒以上且未達2分鐘之情形評價為「△」，將通過所需之時間為2分鐘以上且未達5分鐘之情形評價為「△△」，將通過所需之時間為5分鐘以上之情形評價為「×」，而評價光與溼氣硬化型樹脂組成物之塗佈性(細孔通過性)。 150 mesh filter paper was laid in a filter device with a diameter of 4 cm, and 30 g of each of the light and moisture-curable resin compositions obtained in the examples and comparative examples were subjected to pressure filtration at a pressure of 0.2 MPa, and the passage time was evaluated. The case where the time required for passing is less than 20 seconds is evaluated as "◎", the case where the time required for passing is 20 seconds or more and less than 30 seconds is evaluated as "○", and the time required for passing is 30 seconds or more and less than 2 minutes The case is evaluated as "△", the time required for passing is 2 minutes or more and less than 5 minutes is evaluated as "△△", and the time required for passage is 5 minutes or more as "×", On the other hand, applicability (pore transmittance) of the light and moisture-curable resin composition was evaluated.
(形狀保持性) (Shape retention)
將實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物吸取至2mL之TERUMO注射器中，直線狀地塗佈於載玻片上之後，立刻使用高壓水銀燈照射500mJ/cm2之紫外線而使其光硬化，測定線寬(t0)。以相同之方式將所獲得之各光與溼氣硬化型樹脂組成物塗佈於載玻片上，靜置1分鐘 後照射500mJ之高壓水銀燈而使其光硬化，測定線寬(t1)。將t1/t0≧0.9之情形評價為「◎」，將0.8≦t1/t0<0.9之情形評價為「○」，將0.6≦t1/t0<0.8之情形評價為「△」，將t1/t0<0.6之情形評價為「×」，而評價光與溼氣硬化型樹脂組成物之形狀保持性。 Each of the light and moisture-curable resin compositions obtained in the examples and comparative examples was sucked into a 2 mL TERUMO syringe, applied straight on a glass slide, and immediately irradiated with 500 mJ / cm 2 of ultraviolet light using a high-pressure mercury lamp. Then, the light was hardened, and the line width (t 0 ) was measured. Each of the obtained light and moisture-curable resin composition was coated on a glass slide in the same manner, and after being left for 1 minute, a high-pressure mercury lamp of 500 mJ was irradiated to light-harden, and the line width (t 1 ) was measured. The case where t 1 / t 0 ≧ 0.9 is evaluated as “◎”, the case where 0.8 ≦ t 1 / t 0 <0.9 is evaluated as “○”, and the case where 0.6 ≦ t 1 / t 0 <0.8 is evaluated as “△”. ", The case where t 1 / t 0 <0.6 was evaluated as" × ", and the shape retention of the light and moisture-curable resin composition was evaluated.
(接著性) (Adherence)
使用藥匙將約0.2mL之實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物於載玻片上塗佈為0.5cm之圓形，利用高壓水銀燈照射500mJ/cm2之紫外線而使其光硬化。其後，將載玻片貼合，於貼合面上放置10g之重物，靜置16小時，獲得接著性評價用樣品。圖1中表示自上方觀察接著性評價用樣品之情形時之模式圖(圖1(a))、及自側面觀察接著性評價用樣品之情形時之模式圖(圖1(b))。 Using a medicine spoon, approximately 0.2 mL of each of the light and moisture-curable resin compositions obtained in the examples and comparative examples were coated on a glass slide as a 0.5 cm circle, and 500 mJ / cm 2 of ultraviolet light was irradiated with a high-pressure mercury lamp. And make it light hardened. Thereafter, the slide glass was bonded, and a weight of 10 g was placed on the bonding surface and left for 16 hours to obtain a sample for evaluation of adhesion. Fig. 1 shows a schematic diagram when the sample for adhesiveness evaluation is viewed from above (Fig. 1 (a)) and a schematic diagram when the sample for adhesiveness evaluation is viewed from the side (Fig. 1 (b)).
將所獲得之接著性評價用樣品放入85℃、85 RH%之恆溫恆溼烘箱中，且相對於地面垂直地懸掛10g之重物，靜置24小時。將靜置24小時後之偏移為1mm以下之情形評價為「○」，將超過1mm且為3mm以下之情形評價為「△」，將超過3mm之情形評價為「×」，而評價光與溼氣硬化型樹脂組成物之接著性。 The obtained sample for adhesiveness evaluation was put into a constant temperature and humidity oven at 85 ° C and 85 RH%, and a weight of 10 g was hung vertically from the floor, and left to stand for 24 hours. The case where the deviation after standing for 24 hours was 1 mm or less was evaluated as "○", the case where the deviation was more than 1 mm and 3 mm was evaluated as "△", and the case where the deviation was more than 3 mm was evaluated as "×", and the light and Adhesiveness of moisture-curable resin composition.
(黏度及搖變度) (Viscosity and shake)
使用錐板型黏度計(東機產業公司製造，「VISCOMETER TV-22」)，於25℃、1rpm之條件下對實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物測定黏度。 Using a cone-plate viscometer (manufactured by Toki Sangyo Co., Ltd., "VISCOMETER TV-22"), each light and moisture-curable resin composition obtained in the examples and comparative examples was measured at 25 ° C and 1 rpm. Viscosity.
又，對於實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物，藉由將利用錐板型黏度計於25℃、1rpm之條件下測定出之黏度除以利用錐板型黏度計於25℃、10rpm之條件下測定出之黏度而算出搖變度。 In addition, for each of the light and moisture-curable resin compositions obtained in the examples and comparative examples, the viscosity measured by using a cone-plate viscosity meter at 25 ° C and 1 rpm was divided by the cone-plate type The viscosity meter measures the viscosity at 25 ° C and 10 rpm to calculate the degree of shake.
(柔軟性) (Softness)
對於實施例及比較例中所獲得之各光與溼氣硬化型樹脂組成物，藉由 利用高壓水銀燈照射500mJ/cm2之紫外線而使其光硬化，其後，藉由放置一晚而使其溼氣硬化。對於將所獲得之硬化物沖裁為啞鈴狀(「JIS K 6251」中所規定之6號形狀)而獲得之試驗片，使用拉伸試驗機(島津製作所公司製造，「EZ-Graph」)，於25℃以10mm/min之速度拉伸，將伸長50%時之力作為拉伸彈性模數而求出。 The light and moisture-curable resin compositions obtained in the examples and comparative examples were light-cured by irradiating 500 mJ / cm 2 of ultraviolet light with a high-pressure mercury lamp, and then allowed to stand for one night to make them hard. Moisture hardens. For a test piece obtained by punching the obtained hardened product into a dumbbell shape (No. 6 shape specified in "JIS K 6251"), a tensile tester (manufactured by Shimadzu Corporation, "EZ-Graph") was used. It was stretched at 25 ° C at a speed of 10 mm / min, and the force at 50% elongation was determined as the tensile elastic modulus.
根據本發明，可提供一種形狀保持性、接著性、速硬化性、及塗佈性優異之光與溼氣硬化型樹脂組成物。又，藉由本發明，可提供一種使用該光與溼氣硬化型樹脂組成物而成之電子零件用接著劑及顯示元件用接著劑。 According to the present invention, it is possible to provide a light and moisture-curable resin composition excellent in shape retention, adhesion, rapid curing, and coatability. Furthermore, according to the present invention, it is possible to provide an adhesive for electronic parts and an adhesive for display elements using the light and moisture-curable resin composition.
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| WO2015146873A1 (en) * | 2014-03-26 | 2015-10-01 | 積水化学工業株式会社 | Light-/moisture-curable resin composition, electronic component adhesive, and display element adhesive |
| WO2015174371A1 (en) * | 2014-05-13 | 2015-11-19 | 積水化学工業株式会社 | Photo- and moisture-curing resin composition, adhesive for electronic parts, and adhesive for display element |
| CN105814095B (en) * | 2014-05-30 | 2019-03-22 | 积水化学工业株式会社 | Light moisture-curable resin combination, electronic component-use bonding agent and display element bonding agent |
| JP6023359B2 (en) * | 2014-11-13 | 2016-11-09 | 積水化学工業株式会社 | Cured body, electronic component, and display element |
| KR102494910B1 (en) * | 2014-12-26 | 2023-02-01 | 세메다인 가부시키 가이샤 | Photocurable composition |
| JP6703409B2 (en) * | 2015-02-10 | 2020-06-03 | 積水化学工業株式会社 | Light moisture curable resin composition and heat conductive adhesive |
| CN107075061B (en) * | 2015-04-09 | 2021-08-24 | 积水化学工业株式会社 | Light-moisture-curable resin composition, adhesive for electronic component, and adhesive for display element |
| JP6697306B2 (en) * | 2016-03-31 | 2020-05-20 | ハリマ化成株式会社 | Photocurable composition with moisture curing, conformal coating agent and cured product |
| US20190292347A1 (en) * | 2016-11-30 | 2019-09-26 | Hitachi Chemical Company, Ltd. | Two-part curable urethane composition |
| WO2019035411A1 (en) * | 2017-08-18 | 2019-02-21 | 積水化学工業株式会社 | Moisture curable resin composition, adhesive for electronic components, and adhesive for display elements |
| WO2019124494A1 (en) | 2017-12-22 | 2019-06-27 | 積水化学工業株式会社 | Curable resin composition, cured article, electronic components and assembly components |
| WO2019203277A1 (en) * | 2018-04-19 | 2019-10-24 | 積水化学工業株式会社 | Curable resin composition, cured body, electronic part and assembly part |
| JPWO2020085284A1 (en) * | 2018-10-23 | 2021-10-07 | 積水化学工業株式会社 | Curable resin composition and cured product |
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| JP2004018621A (en) * | 2002-06-14 | 2004-01-22 | Nippon Shokubai Co Ltd | Radical-hardenable urethane resin composition |
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| KR102199885B1 (en) | 2021-01-07 |
| TW201518332A (en) | 2015-05-16 |
| KR102352334B1 (en) | 2022-01-17 |
| TWI680145B (en) | 2019-12-21 |
| JP5845362B2 (en) | 2016-01-20 |
| KR102323651B1 (en) | 2021-11-08 |
| CN105637001A (en) | 2016-06-01 |
| JP6427089B2 (en) | 2018-11-21 |
| TW201927845A (en) | 2019-07-16 |
| CN105637001B (en) | 2019-10-01 |
| JP2016029186A (en) | 2016-03-03 |
| KR20210002763A (en) | 2021-01-08 |
| KR20210002764A (en) | 2021-01-08 |
| WO2015056717A1 (en) | 2015-04-23 |
| JPWO2015056717A1 (en) | 2017-03-09 |
| KR20160073941A (en) | 2016-06-27 |
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